CHEBI:44137 - tiamulin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name tiamulin
ChEBI ID CHEBI:44137
Definition A carbotricyclic compound that is pleuromutilin in which the hydroxyacetate group is replaced by a 2-{[2-(diethylamino)ethyl]sulfanyl}acetate group. An antibacterial drug, tiamulin is used in veterinary medicine (generally as its hydrogen fumarate salt) for the treatment of swine dysentery caused by Serpulina hyodysenteriae.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:29695
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C28H47NO4S
Net Charge 0
Average Mass 493.74200
Monoisotopic Mass 493.323
InChI InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3/t19-,20+,22-,24+,25+,26-,27+,28+/m1/s1
InChIKey UURAUHCOJAIIRQ-QGLSALSOSA-N
SMILES CCN(CC)CCSCC(=O)O[C@@H]1C[C@@](C)(C=C)[C@@H](O)[C@H](C)[C@]23CCC(=O)[C@H]2[C@@]1(C)[C@H](C)CC3
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tiamulin (CHEBI:44137) has functional parent Pleuromutilin (CHEBI:8269)
tiamulin (CHEBI:44137) has role antibacterial drug (CHEBI:36047)
tiamulin (CHEBI:44137) is a carbotricyclic compound (CHEBI:38032)
tiamulin (CHEBI:44137) is a carboxylic ester (CHEBI:33308)
tiamulin (CHEBI:44137) is a cyclic ketone (CHEBI:3992)
tiamulin (CHEBI:44137) is a organic sulfide (CHEBI:16385)
tiamulin (CHEBI:44137) is a secondary alcohol (CHEBI:35681)
tiamulin (CHEBI:44137) is a semisynthetic derivative (CHEBI:72588)
tiamulin (CHEBI:44137) is a tertiary amino compound (CHEBI:50996)
tiamulin (CHEBI:44137) is a tetracyclic diterpenoid (CHEBI:52557)
IUPAC Name
(3aS,4R,5S,6S,8R,9R,9aR,10R)-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl {[2-(diethylamino)ethyl]sulfanyl}acetate
INNs Sources
tiamulin WHO MedNet
tiamulina WHO MedNet
tiamuline WHO MedNet
tiamulinum WHO MedNet
Manual Xrefs Databases
C12065 KEGG COMPOUND
D06127 KEGG DRUG
DE2248237 Patent
MUL PDBeChem
Tiamulin Wikipedia
US3919290 Patent
View more database links
Registry Numbers Types Sources
55297-95-5 CAS Registry Number KEGG COMPOUND
55297-95-5 CAS Registry Number ChemIDplus
7348837 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15013817 PubMed citation Europe PMC
16253666 PubMed citation Europe PMC
25592328 PubMed citation Europe PMC
3170319 PubMed citation Europe PMC
3686511 PubMed citation Europe PMC
Last Modified
30 July 2015